A Wager
by Clare4533
Summary: Regina and Hook get drunk after returning from Never Land, in their drunken state they make a bet for Emma Swans heart...well really who can sleep with her first. Who do you think will win? Doesn't follow storyline after Never Land: Swan Queen
1. Prologue

Prologue

It had started off as a drunken dare between two newly friends. Regina and Hook had decided to share a bottle of rum after returning from Never Land victorious. It was Hook that brought the subject of Emma Swan up, he was wallowing in the fact that Emma had turned him down, saying that she didn't want to date anyone after losing Neal.

Regina laughed at his wallowing, and stole the remainder of his rum, she too had been harbouring a massive crush on Miss Swan since the first time they met on the mayors doorstep.

"I should try and get her! You know like whoo her ya know lass?" Hook drunkenly says while trying to take the rum bottle off of Regina, who quickly snaps it away from him.

"I don't think you're her type pirate!" Regina spits out at him, before downing the remainder of the bottle.

"Why do you care anyway?! It's not like you have a chance with her anyway!" He snaps while trying to stand up, he only ends up failing and falls back down with a hard thump.

"And that makes you think that I want a chance with Miss Swan?" Regina challenges him.

"Oh come on! The long gazes, the small and simple touches! You want her bad and she's either she's too naive to notice it or she just doesn't want to!" He shouts with all his might. Regina acts quickly and covers his mouth before any more nonsense comes out of it.

"Clearly you are too drunk to function, it's time to put you to bed, that or throw you overboard." Regina says, whispering the last part to herself.

"A wager!" He shouts, throwing his hand up into the air.

"What kind of wager?" Regain asks curiously.

"I wager that you can't get Swan into bed before I can..." He says, looking pleased with himself. Thinking that he has the upper hand in this deal.

"And what does the winner get?" Regina asks curiously.

"The other has to back off and move on...you in?" He asks, raising his eye brow at her while sticking out his good hand for a hand shake.

"Deal," Regina pushes his hand away and stands up, she half turns to Hooks and says before exiting the boat "may the battle commence pirate."

Regina took the long way home that night, carefully she planned just how she was going to win the heart of Miss Swan and finally have her happy ending, although a part of her feared that it would come back and bite her as it hand with Daniel. But nonetheless she wasn't going down without a fight!

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I know this is short but trust me it's only the beginning! Please leave a review and let me know what you thought of this new fic!


	2. Chapter 1

**At long last here is the first real chapter of this story. Hope you enjoy it and as always feel free to favourite, follow and leave me a review letting me know what you thought of the first official chapter. I love reading all of your reviews!**

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It had been Henry's fault that she had been running late this morning. He was the one that had insisted that he wasn't going to school so Emma had to spend the whole morning trying to get him out of his bed and into school. This then made her almost an hour late for work. Not that she particularly worried, she knew that Regina had lightened up since they rescued Henry from Never Land together. The only real downside to her being late was that she would not have enough time to enjoy her usual morning hot chocolate in granny's, she guessed that that would have to wait until later.

As soon as she walked into the sheriff's station her senses were overwhelmed by the strong smell of granny's hot chocolatpee with the faint smell of cinnamon. She turned the corner to find none other than Regina Mills, the woman she had just been thinking about a few moments ago leaning against her desk with two take away cups in hand.

"Morning sheriff, I thought you could use a hot drink on this cold morning." Regina said while Emma slowly walked over to the older woman.

"Thanks..." Emma said before slowly taking the cup off of her, there hands brush against each other's, making Regina smile shyly. "It's not laced in position again right?" Emma questioned before trustingly taking a small sip of the now coldish hot chocolate.

"That was one time Miss Swan, I've changed since then. If I wanted you dead I would do so, but not with position." Regina winked before taking a sip of her luke warm latte. "It has however cooled down seeing as you are late for work once again Miss Swan."

"You can blame your son for that! Has he always been this hard to get out of bed?" Emma asked before taking a large gulp of her luke warm hot chocolate, even if it wasn't piping hot like she usually get it.

"Why is he my son when he does something bad?" Regina said sternly to the blonde woman before throwing her half empty coffee cup into the bin.

"You know that's not what I meant Regina!" Emma joked with the older woman before setting her cold hot chocolate on top of the table.

"I know Miss Swan." She smiled wholeheartedly before looking down at the coffee cup on the sheriff's desk, _'Maybe bringing her hot chocolate in the morning knowing fine rightly that she has never been on time since she got the job was a bad idea...'_ Regina thought to herself before meeting Emma's gaze again.

"I'm sorry that your hot chocolate is cold, if I had of known that you were running late I would have waited." Regina said while smiling shyly at the blonde.

"You don't have to apologise, Regina. But if you are so upset about it then you can make it up to me by buying me another at lunch..." Emma suggested, she had been trying to spend as much time with Regina as she could, mostly for Henry's benefit. Both women knew that it annoyed him when the two women were at each other's throats about one thing or another.

The mayor stared at Emma unsure what her true intentions were about what she was proposing.

"We could even take that time to go over those budget reports you are always moaning about." Emma smiled the woman who still still staring at her.

"That sounds like a plan Miss Swan, I'll meet you at granny's around 1ish?" She questioned, while leaning over Emma's desk to grab her coat she had discarded when she first came into the sheriff's office.

"1ish it is then. Thanks again for the coffee Madam Mayor." Emma said as she walked Regain to the door of the sheriff's office.

"Try not to be late Miss Swan..." Regina said sternly before making her way out of the office.

Emma tried her best to keep an eye on the clock as she waited for 1 o'clock to come around so she could go and have lunch with Regina. Emma would never actually admit this to the older woman, but she actually enjoyed her company. When she wasn't trying to kill her of course and when it actually came down to it, Regina was kind of the only friend she had in Storybrooke that didn't speak to her just because she was Snow White's daughter.

It was quarter to one when Emma decided to leave her office, determined that she wasn't going to be late for her lunch with the Mayor. When she walked into Granny's diner she was surprised to find it almost empty, except for a few dwarfs sitting at the counter and Hook sitting in the booth furthest away from the door. _'Great'_ Emma thought as she went to take a seat with her back to Hook at the booth closest to the door. She had been doing everything in her power to avoid the pirate since they came back from Never Land, the man seriously didn't know how to take no for an answer. Even after brutality rejecting him in Never Land he still kept asking and asking.

"Morning Swan..." Emma rolled her eyes and looked up and the scruffy looking pirate staring down at her. "Mind if I take a seat?" He asked while pointing to the empty seat in front of her that was meant for Regina with his hook.

"Sorry it's taken, what do you want Hook?" Emma asked forcefully, she just wished that Regina would hurry up and get here so she didn't have to sit through one of his declarations of love again.

"Have your imaginary friends come to have lunch again Swan?" He joked but Emma simply rolled her eyes yet again at the man.

"What do you want Hook?" Emma asked again while smiling this time at the man.

"I want another chance to prove that I can be what you have been looking for all these years." Hook said sounding cheesy like always.

"Fine..." Emma said without changing her facial expression. Hook however having been used to Emma rejecting him so often started to go on a rant about why she should give him a chance.

"No! Not again Swan, I am a good man and that's what you and the boy need you need someone who is going to be there an..." Emma hit him on the stomach to finally shut him up.

"I said yes you idiot!" Emma said while laughing at the mumbling pirate.

"Are you serious Swan?" He asked while smiling at the blonde haired woman.

"I'm agreeing to one date! That's all! If and this is a big if, if it goes well I might consider a second. Do you understand?" She asked and all the love struck pirate could do was nod in agreement.

"Ahh Miss Swan I see that you are actually on time for once." Emma's head shot over to see Regina enter Granny's and effortlessly slide into the seat facing her. "Is there something we can help you with pirate?" Regina said acknowledging Hook's presence at the table.

"I was just confirming my date with Swan before you interrupted. How does 7 tomorrow night sound?" He turned his attention away from Regina, to face Emma once again.

"Sounds fine to me, now Hook if you don't mind Regina and I actually have a lot of work to get through..." Emma hinted at him that it was time to leave.

"Right sorry. See you around Swan...your Highness." He smirked at Regina before exiting Granny's.

"So you and the pirate?" Regina asked, trying to hide the hurt in her voice. If only she had of been able to ask Emma out earlier like she had planned.

"I don't know, he's been asking me out for a while now and I guess I just finally decided to give it. I doubt it will go anywhere to be honest." Emma smiled at the Mayor before lifting up the menu. This meant that she failed to notice the giant grin that was currently on the Mayor's face because of what she had just said. _'So I still have a chance then!'_ Regina internally screamed before picking up her own menu to hide the smirk.


	3. Chapter 2

**Hope you enjoy it and as always feel free to favourite, follow and leave me a review letting me know what you thought of this chapter. Also thanks for all the reviews, favourite's and follow's I have already received I really appreciate it!**

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The rest of the day for Emma went completely interruption free, she was left alone in her office to get a head start on all the paperwork Regina had led on her while at their lunch together. Emma was pleasantly surprised that her lunch with Regina went off without a hitch, they laughed and chatted about absolutely nothing while they waited for their food to arrive and then after that they talked work and budget reports for the rest of the afternoon, until Regina had to head back to the office to get up to date with her own paperwork.

This left Emma to her thoughts about whether or not she was doing the right thing by going on this date with Hook, she feared that this might upset Henry even more since it hasn't been long since he lost his dad. So she made the decision that she would talk to him first before actually going on the date tomorrow night.

"Hey, kid!" Emma shouted before running over to meet Henry at the school gate. The tall boy was currently standing beside Mary Margaret and David who had offered to pick Henry up.

"Mom? I thought David was picking me up." Henry said confusingly.

"Yeah well I finished early so I thought you and I could go down to the beach for a while, maybe get an ice cream?" Emma suggested while bumping shoulders with her son.

"Sounds good to me! See you later!" He said to Mary Margaret and David before walking away with Emma towards the beach. Leaving Mary Margaret and David smiling at their daughter and grandson walking away.

"Did you actually get your work done or are you just avoiding my mom?" Henry asked while walking beside Emma with a large chocolate chip ice cream in hand.

"Believe it or not, I actually finished everything!" She laughed before taking a big lick of her strawberry ice cream.

"Okay, I'll believe you this time...It's been a while since we've done this." Henry looked over to Emma who simply smiled at him.

"Yeah, I figured that after everything that's been going on lately we could use a catch-up. We haven't really had a chance to catch up since we got back." Emma stopped and gestured for him to take a seat on the bench that faces the sea. Silently Henry takes a beside his mother on the bench. "We haven't had a chance to talk about your dad..." Emma said quietly, but not too quiet so Henry could still hear her.

"I miss him, mom..." Henry replied quietly without looking at Emma.

"I miss him too Henry…" Emma said, leaving it at that. She knew that this was not the right time for either of them to be talking about this, let alone for Emma to be talking about Hook to Henry.

"I don't think he'd want us to be like this…" Henry said surprising Emma.

"What do you mean Henry?" Emma asked concern creeping onto her face.

"He wouldn't want us sitting here and moping…he'd want us to move on and enjoy our lives," Henry explained while placing his hand on top of Emma's.

"You know for someone who hates school so much you sure are a smart ass!" Emma joked before pulling him in for a long overdue hug.

"Mom…I know what you wanted to talk to me about." Henry said while looking up at Emma.

"What?" Emma questioned the boy.

"I saw you talking to my mom earlier…you don't want me to stay with you anymore do you?" Henry questioned sadly.

"What?! Henry that is not what is going on! Your mom and I were just going over budget reports! Of course, I want you, you're my son Henry and nothing is going to change that okay!" Emma exclaimed before pulling Henry in close for a bone crushing hug.

"What did you want to talk to me about then?" Henry asked while wiping a tear away from his cheek.

"I kind of agreed to go on a date with Hook…but only if you are okay with it. I won't go if you don't want me to Henry." Emma quickly explained.

"I think it's a good idea I guess…it's what dad would have wanted," Henry smiled proudly at his mother, before resuming to eat his almost melted ice cream.

"It's only one date, it's not like we are getting married Henry!" Emma joked before returning back to her ice cream as well.

Regina sat in her home office nursing a glass of strong apple cider and going over the budget reports from the sheriff's department that Emma had surprisingly sent over on time for once. Even though she was going over paperwork, her mind was far from work. All she was able to think about was how she was going to win Emma over. Not because of this stupid bet with Hook, but because she knew that right from the first time she met her on her doorstep a few months ago that she was the one that she was meant to be with and there was no way in hell was she going to let some pirate who only wants a quick lay get to her first.

She had to think of something smart and fast, something that wouldn't give away her feelings just yet. _'I could always take her up on her family night offer'_ Regina thought to herself before smiling wickedly. She knew exactly how she was going to do this, but first she may need some help.


	4. Chapter 3

**Hope you enjoy it and as always feel free to favourite, follow and leave me a review letting me know what you thought of this chapter. Also thanks for all the reviews, favourite's and follow's I have already received I really appreciate it!**

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Mary Margaret woke to the loud banging on her apartment door, with one eye opened she listened to see if anyone would get it, but seeing as it was the weekend and everybody that lived in her extremely small apartment were all dead to the world when they were asleep, she knew that it would be her that would have to get out of bed to get the door.

Forcefully she pulled forward the duvet not caring if it got pulled off David as well, before she made her way to the door, fully dressed in her bunny rabbit pyjamas with matching bunny slippers.

"What?!" She shouted as she violently opened the door, only to find the former Evil Queen standing with what looked to be a take out bag from Granny's and 5 take out coffee cups.

"Well good morning to you too dear, mind if I come in? I brought breakfast!" She said excitedly while holding up the take out bag.

"Umm, sure come in. I'll just go and wake everyone up..." Mary Margaret said weirdly before heading to Emma's room to wake her up before trying to wake Henry and David up.

This left Regina alone in the kitchen/living room, carefully she set the bags and cups down on the counter before trying to find a large enough plate to hold all the pastries she had bought. Emma was the first to arrive downstairs, Regina saw her before Emma saw Regina. Regina noted all the things she had never seen in the woman before now, like the way that her hair sits when she's just gotten out of bed, or the way her legs look in those pyjama shorts.

"Regina?" Emma questioned, while walking over to the older woman. "So Mary Margaret was being serious, I thought she was just trying to get us all out of bed..." Emma said before laughing to herself mostly.

"This is for you...I figured since the one I got you yesterday was cold and since you didn't order one at lunch yesterday that I'd bring you the replacement that I promised." Regina said shyly before handing the piping hot cup to a very sleepy looking Emma.

"Thanks Regina but you didn't have to do all of thi...is that a bear claw?!" Emma quickly leaned over past Regina to the plate that was sitting behind her to grab the pastry. This action had Emma practically on top of Regina, not that Regina minded. Truly if she had the guts she would just grab her and kiss her there and then, but she doesn't so she simply held her breath and waited for the blonde to remove herself.

It took a moment for Emma to realise how close she was to the older woman, quickly she pulled away from her and took a large bite out of the bear claw while avoiding eye contact with Regina to hide the small hint of blush that was starting to form on her cheeks.

"So...tonight's the big date then." Regina said awkwardly while trying to hide the sound of hurt in her voice.

"Umm yeah...I'm not too sure about it though. I talked to Henry about it yesterday and he seemed to be fine with it but I'm not sure I believe him just yet...oh morning sleepy head." Emma suddenly said while an extremely tried Henry followed by David and a pissed off Mary Margaret.

"Morning Mom and...Mom." Henry said while his eyes landed on Regina.

"Morning dear, I brought you your favourite." Regina smiled widely at him before holding out the smallest of the coffee cups. "There is plenty for everyone...help yourselves." Regina said while moving over to where Emma was standing with a half eaten bear claw in hand.

"Thanks Regina, that was really nice if you." David said in a sleepy tone before lifting one of the coffee cups up to his lips.

"Yeah thanks for the wake up call, God knows how I would have gotten them up if it wasn't for you." Mary Margaret smiled before ripping a doughnut in half.

"So mom what brings you here?" Henry asked from the other side of the kitchen with a semi full mouth of food.

"Henry don't talk with your mouth full!" "Henry swallow first!" Both women said at the same time to their son.

"Sorry..." He said quietly while Mary Margaret and David laughed at the scene that was unfolding in front of them.

"To answer your question Henry I'm here to offer my services to Miss Swan...I assume you don't have a babysitter for tonight?" Regina asked rhetorically.

"What's tonight?" Mary Margaret asked.

"I agreed to go on a date with Hook, it's no biggie." Emma said before taking a large drink of her hot chocolate.

"As I was saying, seeing how you don't have a babysitter for Henry yet I was thinking that maybe I could take him for the night. If you wanted you could pick him up afterwards or he could stay over. It's up to you...and Henry of course." Regina said while smiling at Henry. They haven't really been able to spend any time together since returning from Never Land, so this would definitely mean a lot to Regina if Emma agreed.

"That'd be great Regina thanks, but it is up to Henry. What do you say kid?" The attention from everyone in the room is down on Henry, who simply shrugs his shoulders in response.

"I guess that could be cool...it would be nice to be able to spend sometime together again." Henry said to Regina who can't seem to wipe the giant smile off her face, not that she would even want to at this moment in time.

"I guess it's settled then, you can drop Henry off tonight and then pick him up tomorrow if that's okay with you." Regina asked Emma happily.

"Sounds good to me..." Emma smiled at the older woman before messing up Henry's hair with her free hand.

The former Evil Queen and the Charming's seemed to fall into a surprising civil conversation with each other while Emma and Henry headed upstairs to get changed out if their pyjamas before joining the conversation once again.

Regina had stayed at the Charming's apartment for about two hours before she said her goodbye's to everyone and headed toward the supermarket to get all the supplies she needed to cook up Henry's favourite meal: Lasagna. She was thankful that Emma had agreed to let her have Henry for the night. Tonight would be the start of probably her best plan yet...the plan to win the heart of the town's saviour.

Emma had been rummaging through her closet for something to wear when her mother quietly came into her room and took a seat on her bed to wait for her daughter to acknowledge her presence.

"Okay this one or this one?" Emma spun around with a pink dress in one hand and a red one in the one.

"The pink one is nice...when were you going to tell me about your date with Killian?" Mary Margaret asked, changing the subject. She had not wanted to get into this when Regina and Henry were there at breakfast, but not Regina was gone and Henry was in the shower, this was the perfect time to confront her about this.

"I don't know, I was only worried about how Henry felt about it, I didn't think that I had to inform my parents that I've known for a total of two seconds of who I was dating!" Emma snapped at her mother. After replaying the words in her head Emma instantly regretted what she had said to the woman. "I'm sorry...I didn't mean to snap like that. It's just I'm not used to the whole having someone who cares about me thing." Emma admitted to her mother while she sat down beside her silent mother.

"I understand, but you know that your dad and I only want what's best for you..." She squeezed Emma's leg before walking towards the door. "Emma, you can't run away from your feelings forever...eventually you'll realise that." Mary Margaret said before heading down the stairs.


	5. Chapter 4

**Hope you enjoy it and as always feel free to favourite, follow and leave me a review letting me know what you thought of this chapter. Also thanks for all the reviews, favourite's and follow's I have already received I really appreciate it!**

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Emma didn't understand what her mother had been talking about before, as far as Emma knew she had no feelings for anyone in that way. She did care about people obviously, there was Henry, her parents, Regain, hell even Hook on a good day. But she was still yet to meet someone in Storybrooke that she could even consider a life with. I mean sure she was about to go on a date with Hook, but she knew nothing serious would ever happen to them. At most they would probably sleep together a few times and then call it a day.

"Mom! What time are w…wow you look…different." Henry said, shocked at how his mom looked. The young boy had only ever seen in mom in a dress once and that was well over a year ago.

"Good different I hope," Emma smiled shyly at him.

"Definitely!" He smiled at his mother before remembering the reason he came into his mother's room. "Umm, what time are we going to mom's at?"

"In about 10 minutes so make sure you have everything you need!" Emma said while looking down at the watch Neal stole for her years ago.

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Regina was in the middle of making her homemade tomato sauce when the doorbell rang, the former Evil Queen suddenly felt jolts of electricity racing through her body. She couldn't wait to have her son under her roof once again. However, she was also worried about how he might react to her confession about Miss Swan, Regina had been wanting to talk to Henry about the saviour for a while now, she simply couldn't find the right time that was until tonight, she was finally going to tell someone other than that stupid pirate.

When the Mayor opened the door she was treated to Miss Swan in an almost skin tight hot pink dress that came to just above her knees. She could slowly feel her insides catch on fire and her throat suddenly became bone dry.

"Wow…" She said so quietly that only herself and Emma could hear. Henry, however, was none the wiser.

"Bye, mom! Have fun on your date!" Henry said before kissing the blonde woman on the cheek and running up the stairs to his old bedroom.

"Are you okay Regina?" Emma asked with a worried expression painted on her face. The mayor coughed slightly and tried to regain her composer before speaking to the younger woman.

"I'm fine…you scrub up quite nicely Miss Swan." The older woman complimented the blonde woman in front of her.

"Is the great and terrifying Evil Queen actually saying something nice about me?" Emma joked with the woman while smiling like a fool. She loved when she was able to be like this with the mayor, it made a change from all their bickering.

"Have fun on your date tonight Miss Swan and I expect to see you here at 12 for Henry." The older woman said while putting on her best mayor voice to try and hide her obvious attraction to the younger woman.

"Of course, Madam Mayor…see you then," Emma smiled shyly before walking away from the mayor.

Regina couldn't wait to close the door and let out a breath that she didn't even she know she was holding.

"Mom, are you okay?" Henry asked from the top of the stairs. The mayor quickly straightened up her posture before walking over to the large staircase.

"It's rude to spy Henry…but I'll let you away with it if you come down and help me finish dinner." She suggested while smiling at the boy.

"I think I can manage that!" He said excitedly before walking down the stairs to help his mother.

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Emma sat nervously in the restaurant waiting for the one-handed pirate to show up. She had already been waiting alone like a fool for almost an hour when Hook finally showed up.

"Sorry Swan, I lost track of time while I was down at the Rabbit Hole. Can you forgive me, love?" Hook leant in to kiss the blonde woman on the cheek but she simply moved away.

"Do you know how long I've been waiting here, Hook?! I've been sitting here like an idiot for nearly an hour!" Emma shouted at the man.

"I'm sorry Swan, let's just forget about it and enjoy our night love." The pirate suggested.

"Are you kidding me?! You're lucky I haven't decked you yet!" Emma snapped at the man, who looked like he didn't actually give a crap about what the blonde was saying.

"Swan I made a mistake! Don't let it ruin our night."

"No! I told you that you had one chance and you blew it!" Emma quickly got up and stormed out of the restaurant.

The blonde woman was furious, she couldn't believe that Hook would have done that, essentially after going on and on about them going out on a date.

Emma didn't want to go home; she knew that her parents would give her the whole 'I told you he hadn't changed' speech. So she decided to drown her sorrows in Granny's.

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After a peaceful dinner, Regina and Henry cuddled up on the sofa to watch the new Spiderman movie that he had brought over from the loft. Regina was yet to speak to the boy about his blonde mother but she knew that it had to be done, especially after she heard that Emma had asked Henry what he thought about her dating again. The older woman knew that if she was ever to have a chance with Emma then she was going to need their son on her side.

"Hey Henry, can I talk to you about something?" Regina asked, pulling the boys concentration away from the television.

"Sure, what's up mom?" He asked while Regina paused the movie to get his full attention.

"It's about Miss Swan...well you see, I kind of well not kind of, I know that she's...maybe that might be too strong of a word. Miss Swan is well; she is..."

"Beautiful? Special? Your true love? All of the above?" Henry questioned the mayor.

"I... well. Yes...how did you know?" Regina asked sounding worried. Had she been making her feelings for Miss Swan so obvious that their 12-year-old son had picked up on them?

"I was just kidding! Wait do you really think that mom is your true love?!" The boy asked excitedly.

"I think so Henry...so you're not opposed to the idea?" Regina asked nervously.

"Did you think I would be?! This is going to be so awesome! When are you going to tell her?!...Wait she's on a date with Hook" Henry suddenly went from being extremely happy to being sad at the thought of his mom being with someone other than his adoptive mother.

"I know dear...that's why I can't tell her. Not yet at least, if she and the pirate are happy then I'll let them be happy, but if not then I'll tell her. But...I might need your help, you up for it?" Regina raised her eyebrow at him.

"I'd rather her be with you than Hook any day so, yeah I'm in. What's the plan?" Henry asked before moving closer to listen to what Regina had to say.

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Emma had spent the last few hours cursing the pirate's name and drinking almost her weight in whiskey in Granny's, that was until Granny cut her off and told her to head home. That was something and definitely didn't want to do at this moment in time so the saviour simply began to walk the streets of Storybrooke, until she found herself outside of a house that she knew all too well. Without even realising what her feet were doing the drunk blonde made her way up the path that led to house No. 108. Without caring about the time she knocked three times as loud as she could, until the mayor came to the door wearing no more than a black silk robe and a confused look on her face.

"Miss Swan what are you doing here at this hour?" She whisper shouted so she didn't wake Henry.

"It's 12..." Was all Emma was able to say before she felt the sudden urge to throw up...all over the mayor's flower bed.


	6. Chapter 5

**Hope you enjoy it and as always feel free to favourite, follow and leave me a review!**

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After the saviour had threw up all over the mayor's flower bed, the former Evil Queen the brought the intoxicated sheriff inside and sat her on the sofa.

"I take it your date went well Miss Swan?" Regina asked while walking into the kitchen to grab her a glass of water.

"I wore a dress, Regina! I wore a fucking dress and he didn't even notice!" Emma shouted to Regina.

"He's a stupid pirate Swan!" Regina said as she walked back into the living room to find Emma now passed out on her sofa. "And you deserve way better...maybe one day I'll have enough courage to actually tell you." Regina said quietly before placing a throw over the sleeping blonde.

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 _"Emma dear it's time to wake up..." Emma woke up to see Regina's beautiful brown eyes staring down at her. Emma blinks a few times before smiling sweetly at her wife._

 _"Morning baby..." Emma said quietly before leaning up to kiss Regina._

 _"Mom! I'm hungry!" Henry shouted up the stairs, making Regina pull away from her blonde lover._

 _"No, don't go..." Emma tried to pull Regina back to her, but the older woman worms her way out of her grip._

 _"Someone has to feed our son...you stay in bed and I'll bring you something_ up, _" Regina said while grabbing her black silk robe. "I love_ you _, Emma Swan...I always have." Regina said while smiling shyly at her wife before leaving the room._

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"Mom? What are you doing here?" Emma stirs in her sleep as she hears Henry's voice.

"Henry leave Miss Swan alone...you can go and watch cartoons in the other room," Regina said sternly to their son.

"Regina?" Emma questioned while finally opening her eyes, that are instantly forced shut because of the light in the room and her raging hangover.

"Good morning to you too Miss Swan," Regina said while trying to hide the smile that always seems come across her face when the saviour says her name.

"What the hell happened last night?" The sheriff asked while sitting up, that's when she notices that she is still wearing her dress from her pathetic excuse for a date with Hook last night.

"You got intoxicated and then threw up on my flower bed." The mayor said sternly before handing Emma a bottle of water and a few aspirin tablets. "And you might want to take these, I can only imagine how hungover you are at the moment..."

"Thanks, Regina and I'm sorry about last night, I didn't mean to get that fucked up." Emma quickly said.

"Language Miss Swan , our son is in the next room!" Regina snapped.

"Sorry...again. I should get going my parents are probably wondering where I am." Emma said quietly while getting up off the sofa.

"Why don't you stay for breakfast first?" Regina suggested in an attempt to spend more time with the younger woman.

"That'd be nice...thanks," Emma smiled at her.

"You can go and sit with Henry and I'll go and get breakfast prepared," Regina said before walking away from the smiling woman.

Emma slowly sat back down on the sofa and tried to recall what had happened the night before, she remembered dropping Henry off at Regina's, she remembered joking around with Regina and then she remembered fighting with Hook and that's all, she doesn't know where she went after she left the restaurant and she doesn't remember why she went to Regina's or what time she had arrived. All she knows is that she left her date and then somehow ended up at the mayor's house.

"What the hell happened last night?!" She said to herself before running her hand through her messy hair, before making her way into the second living room where her son sat glued to the TV.

"Morning kid," Emma said while patting Henry's head and sitting down beside him.

"Hey, mom," Henry said not taking his eyes off of the screen. Emma sat back in the seat, she was thankful that the aspirin had finally kicked in. As she watched the TV with Henry, her mind couldn't help but think about the dream she was having. It wasn't the first time she had of dreamt about Regina, it was the first time however that she had ever dreamt about a relationship with the older woman, let alone a dream about being married to her. Emma had never looked at the former Evil Queen in that way, sure she had looked at other women before but Regina in her mind anyway was out of bounds.

"So how was your date mom?" Henry asked, pulling Emma out of her Regina daydream.

"Let's just say I don't think that there will be a second date." Emma half smiled at her son before out of the corner of her eye she saw Regina struggle to walk in with two trays of food. "Here let me help..." Emma quickly got up and took one of the trays off of the older woman before taking a seat once again beside their son who had already eaten his cereal.

The three of them simply sat in the living room watching TV and chatting about nothing for the remainder of the morning, until Henry had to get ready for sword fighting lesson, leaving Regina and Emma alone again. The mayor took this opportunity to talk to the sheriff about budget reports, whereas the sheriff couldn't get her dream out of her mind.

It was around 12 o'clock when Henry was finally ready to leave for his lesson with David.

"This was nice Miss Swan, we should do it again when you are less hungover." Regina joked while both women waited for Henry to grab the rest of his stuff from upstairs.

"Why don't we do lunch sometime this week?" Emma suggested, taking Regina by surprise. The mayor couldn't tell if the younger woman was asking her out or simply trying to be civil because of Henry.

"Why don't we do dinner sometimes?" Regina suggested, pushing the idea of a date with the woman to the back of her mind.

"I was thinking Lunch sometime instead...but if you would rather do dinner that's fine by me," Emma said while smiling shyly at the woman.

"Lunch sounds...nice. I'm free on Tuesday if you are." Regina smiled sincerely.

"It's a date!" Emma said excitedly, making the mayor's eyes widen in surprise. Before Regina had a chance to respond Henry came running down the stairs, shouting about how he is going to be late.

"Henry give your mother a kiss before we go," Emma said to the excited boy.

"I will if you will..." Henry muttered quietly before giving Regina a quick peck on the cheek and running out the door.

"Guess I'll see you ok Tuesday then!" Emma said excitedly before running to meet up with Henry. Leaving Regina to worry about what Tuesday was really about.


	7. Chapter 6

Hope you enjoy and like always please remember to leave me a review and let me know what you thought of this new chapter!

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Both Emma and Regina had made sure to keep busy on the days leading up to their lunch 'date'. Regina had spent the time burying herself in paperwork that wasn't due to be done until the end of the month, whereas Emma spent her time both avoiding Hook and spending time with her newly acquainted parents and her son. Emma had been looking forward to having lunch with Regina, especially after the dream she had while passed out on the mayor's sofa. The dream in question had been replying over and over again in the sheriff's mind, it was no secret to anyone that Emma knew before Henry showed up on her doorstep, that Emma was interested in both men and women, however since coming to Storybrooke she had decided to keep her sexuality on the down low. Emma was afraid of how people would react to her coming out, especially her parents. Emma wasn't even sure that the Enchanted Forest had lesbians and if they did it wasn't likely that anyone knew about them. Emma's Tuesday morning had started off surprisingly pleasant, that was until she walked in to find Hook sitting at her desk.

"Hear me out, love…" Hook said while standing up as soon he saw the blonde sheriff walk into the office.

"Why should I? So you can try and feed me some stupid excuse as to why you thought that getting drunk and then showing up late to our date, a date that you begged for might I add, was the right thing to do!" Emma shouted while slamming her fist onto the desk.

"Swan, I was stupid, is that what you want to hear? I messed up on something that, could have ended up being the best thing to ever happen to me…but I've accepted that I'm only here to say sorry Swan, I'll leave you to get on with your work." Hook confessed, before nodding sadly at the sheriff and exiting the station, leaving the blonde speechless and slightly confused at the way the pirate is acting. She had expected him to blow Saturday night off and ask her out once again, only to do the exact same thing all over again.

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Regina had spent her weekend stressing about her lunch with Miss Swan, she knew that the younger woman couldn't possibly have any interest in her. Emma Swan is the savior after all and Regina is the Evil Queen who tore her away from her parents and forced her to become an orphan her whole life, how could someone possibly want to be with the monster that did that.

"Hey, mom! Are you home?" Regina was startled when she heard her son's voice fill the house.

"Henry? Why aren't you at school?" Regina said as she walked out of her study to see Henry fully dressed in his school uniform.

"I was on my way, but I had to come and see you when ma told me that you two were having lunch today! Why didn't you tell me that Operation Octopus was a go!" Henry said excitedly before pulling his mom into a near bone-crushing hug.

"Henry, it's only lunch…I don't want you getting your hopes up, it's only a work lunch." Regina explained to her son who's face slowly started to sadden.

"But you're going to tell her how you feel, right?" Henry asked, once again getting his hopes up about his two mothers getting together so that they could all be one happy family.

"I'm not sure that's a good idea, Henry, I don't even know if Miss Swan likes me in that way, or women in general," Regina explained, before letting out a huff of frustration.

"But, what if you don't and then she goes on another date with Hook and you lose her forever!" Henry nearly shouted.

"Henry, if that happens then it happens. I can't force Emma to like me the way I like her, I can only try and see if this could work. But I'm not ready for that to happen just yet, do you understand?" Regina asked in a gentler tone this time as she could see the boy was starting to get himself worked up over all of this.

"Mom, please…just tell her for me" The boy begged, while giving his mom the puppy dog face.

"Okay, fine. But if things go badly…I'm grounding you for a week!" Regina fake threatened her son, who simply laughed and threw his arms around his mother once again.

"Things won't go bad, I promise!"

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Regina had been the first one to show up to Granny's Diner this time. She had been so nervous about telling Miss Swan that she has feeling for her, she had never done that before and didn't even know how to approach the topic. Sure she had both men and women confess their undying love for her when she was the Evil Queen, but she knew that they were only saying those things out of fear, not out of love.

"Can I take your order, Mayor Mills?" Red asked as she approached the booth Regina was sitting in.

"No thank you, I'm waiting for someone," Regina said, trying to sound as normal as possible.

"Oh, you're on a date?! I get it, I'll leave you be until your date arrives." Red near enough shouted all over the diner.

"No, it's not a…date" Before Regina could even utter the last word the waitress had skipped off to take someone else's order.

"So…you're on a date then?" Regina nearly jumped out of her skin when she heard the voice of the sheriff behind her.

"Well, if memory serves me right, you did say it's a date…am I wrong?" It was as if all her fears about talking to the woman had vanished and she, at last, knew exactly what she needed to say and how she was going to bring it up, the only question was…how would Emma Swan react?


	8. Chapter 7

Hey guys! I'm back, sorry it's so long since my last update! I've been suffering from writers block, but now I'm back for a while at least. Like always feel free to leave me a review and let me know what you guys think and enjoy!

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Emma was slightly taken aback from how Regina was acting, but she decided to brush it off and enjoy their date…LUNCH. Emma has to keep reminding herself that this is not a date! That terrible evening she spent with Hook was a date, this is no more than a nice lunch between two women that share a child together and just so happen to kinda be related…well not by blood, but still Emma can't just forget that Regina is basically her grandmother…her really beautiful grandmother, okay that is just wrong on so many levels!

"Are you just going to stand there Miss Swan, or are you actually going to join me?" Regain questioned, breaking the blonde sheriff from her really disturbing daydream.

"I'm definitely going to join you, I'm starving!" The blonde said excitedly while taking a seat beside the former Evil Queen herself.

"I assume you'll be having something that is dripping in grease per usual?" The Mayor asked rhetorically, all the Savior could do was smirk in reply.

"You are incorrect Madam Mayor, I was actually considering having a salad today. Have to keep this body looking good, a burger and fries won't help with that." Emma said, lying to the older woman. She actually had no intention of ordering either of those things, in fact, she was really craving a grilled cheese sandwich.

"I'm in shock Miss Swan, however, I do know that…oh, how does Henry say it…oh yes, I do know that you are trying to pull a fast one on me…and since we are on the topic of your body, can I just say that yo…"

"You guys ready to order?" Ruby said interrupting Regina just before she got to the point of her statement.

"Yeah, I'll have the grilled cheese and I'll bet that Madam Mayor will have a kale salad, but you'll have to ask her." Emma teased Regina while Ruby looked to Regina for confirmation.

"I'll have the grilled cheese sandwich as well please Miss Lucas, oh and a tea and hot chocolate for the sheriff, please," Regina said while starring at Emma the whole time.

"Okay, I'll be back soon with your drinks…that is so a date!" Ruby giggled to herself once she knew she was out of earshot.

"I'm not as predictable as you think Miss Swan," Regina said sternly, while Emma smiled shyly at her.

"I don't think that you are predictable Regina, in fact, you surprise me every day. I know you don't hear this often, but you are truly amazing Regina Mills." Emma said, with a faint blush now appearing on her cheeks.

"Feel free to continue Miss Swan, I'm intrigued now." Regina smiled shyly at the goofy blonde.

"Where do I start, you were able to enact an extremely powerful curse, I mean yeah it was in spite of my mother, but it was still pretty epic, oh and you raised our son on your own! You single handily run this town, do I need to go on?" Emma asked making the Mayor look down at the table.

"No, I think you have proven your point, Miss Swan…" Regina smiled brightly at the younger woman, before yet again their lunch was interrupted by Ruby who came over to place their drinks down in front of them.

"Thanks, Rubs…" Emma said while still smiling at the Mayor.

"I think that we should get back to why we agreed to meet for lunch today in the first place, don't you?" Regina suggested, before taking a sip of her tea.

"And what was that Madam Mayor?" Emma asked while blowing on her hot chocolate.

"I'm not too sure, as I recall you just suggested we have lunch together and me being the fool I am agreed," Regina said while laughing slightly along with the sheriff.

"You know; we shouldn't need a reason! From now on, we should get lunch together whenever we want. It's better than waiting for a stupid pirate that doesn't show up, right?" Emma suggested to Regina, who at this moment in time was extremely happy.

"I agree Miss Swan, but now that I think about it there is actually a reason I agreed to this lunch…" Regina said, thinking back to her conversation she had with their son a few hours ago.

"I'm all ears Madam Mayor." The Savior smiled sweetly at the older woman.

"Well you see, umm I've never actually done this before. Okay, Emma…Miss Swan, what I'm trying to say is that you, me and Henry are kind of like a little family now and I guess I just wanted to ask you if you wanted to…."

"Hold that thought…Sheriff Swan?"

"Seriously!" Regina said mostly to herself while drinking her tea to calm herself down.

"Sorry Regina, there's a dog emergency and Pongo hates my dad…"

"It's quite okay Miss Swan, we can finish this another time, why don't you and Henry come over for dinner tonight and we can finish this little conversation," Regina suggested while Emma tried her best to down her hot chocolate.

"Henry has a sleepover tonight…would it be okay if it was just me? My parents are having a date night and I was just going to come here after work." Emma asked, making Regina's heart flutter slightly at the thoughts of being alone with Emma.

"That's fine…seven-ish?"

"Yeah, sounds good to me!" Emma smiled as Ruby appeared with their lunch. "Lunch is on me! Bye Rubs! See ya tonight Regina!" Emma shouted while throwing twenty bucks on the table and grabbing her grilled cheese sandwich right off the plate before running out the door.

"Well, this date was an improvement from her last one," Ruby said while setting Regina's plate down in front of her.

"Not a date…" Regina said while still looking at the spot Emma was in a few seconds ago.

"Keep telling yourself that Madam Mayor!" Ruby commented before walking away to tend to other costumers.


End file.
